Best thing I never had
by Kalenafangirl
Summary: AH/AU. Elena Gilbert is a 23 year old girl living the single life in New York city, wanting nothing but a 'no strings attached' relationship, will she change her mind when she meets Damon Salvatore?  prologue, continues after 5 reviews
1. Chapter 1

**Prologue **

Elena's seat belt violently pierced into her skin as her parent's _Range Rover_ flipped quickly down towards a ditch beside Mystic Fall's Wickery Bridge. Her eyes squeezed shut and broken glass puncturing Elena's skin deep enough to draw small amounts of blood, she had to be dreaming.

"_Elena snap out of it"_, Elena thought, this was just a scary nightmare, there was no way she was in a car crash with her parent's at this moment. "_Wake up" _she thought again. But this wasn't a scary nightmare, this was in fact Elena Gilbert , the 17 year old loner who no one talked to and if she would die from this horrific car crash, no one would remember her either.

The car suddenly stopped and Elena slowly opened her eyes. She was in the back seat, panting, crying hysterically, her mother, Miranda in the front passenger seat was clearly unconscious and her father, Grayson was no where in sight.

Elena was relieved that she could actually unbuckle her seat belt and after doing so she shoved broken door open and fell straight to the ground. Her legs like jelly and the bones in her arms aching, Elena sobbed uncontrollably. She had no idea what to do, there was not a passer in sight. With all the strength she had left, Elena grabbed the door handle and pulled herself up.

Stumbling to the other side of the car, Elena gasped loudly to see her father had been thrown out of the car. Elena ran towards him and looked between her father and the car, the dashboard window was smashed to pieces, she saw visible blood pouring from her mother's head. Elena felt sick with fear. Shaking she examined her father, just hoping for a miracle. No pulse. Elena screamed in between sobs. Then she stopped, she remembered her cell phone in her purse. Elena left her father and ran to the backseat and retrieved her cell phone from her bag.

She dialed 911 as that was the only emergency number she knew, she never in a million years think she would be calling this number and to rescue herself and her family.

"911 what's your emergency?" a female operator asked.

"Um…my parent's car drove into a tree in a ditch by Wickery Bridge and I think they're dead" Elena cried, she couldn't believe the words coming out of her mouth, they couldn't be dead.

"What's your name?" the woman asked.

"Elena Gilbert, please just get someone here" she fell to the ground once again, her head moving in directions just to hope she could see someone around.

"We'll have a paramedic team right with you Elena" the woman said before Elena hung up. Elena encircled her arms around her legs and pulled them up to her chest, she rocked slowly, her make-up smudged, deep cuts on her arm, a trickle of blood making it's from her forehead to her ear. Nothing could prepare Elena for _any _news she was going to receive about her parents.

**AN: This is just to show you what exactly Elena has been through. It does get explained more in further chapters and this IS a 100% Delena story. Please tell me if I should continue. **


	2. Chapter 2

"Elena Gilbert! Are you joking me right now?" Elena's best friend and roommate yelled to her to Elena's room from the kitchen.

"Relax Car, I'll be out in a second!" Elena replied, applying the last bit of make-up needed to complete her 'Sexy Saturday night' look in Caroline's words. Elena strapped on a pair of high heeled, black ankle boots before model walking dramatically to Caroline's sight in their kitchen.

"My god, you look hot!" Caroline eyed her friend before approaching her.

"You think? This isn't too much?" Elena asked, narrowing her eyes. She wore a dark blue lace dress which hugged her slim figure perfectly and her soft eye-make up said 'bedroom eyes' which was exactly what she was going for.

"It's perfect, guys will be drooling over you _tonight_" the curly haired blond nudged Elena's shoulder as they headed out of their apartment into the buzzing city of New York. Tonight was fun night. Elena would not sit at home eating cookie dough and watching _The Notebook_ to cure the pain of her pathetic past relationship break ups, she would get dolled up and get numbers of guys in clubs and hope for the best. She was 23 years old for god's sakes, she need to be enjoying the young life.

"I think we should go to Heat first, there's always hot guys there" Caroline nodded towards a hotspot in a small street.

"That's because most of the guys in there are gay Caroline" Elena explained linking her friend.

"Yeah! Why is it that all the gay guys are the hottest?" she asked. Elena shrugged at the unanswered question that she was sure was asked many of times as they entered the club.

"Oh, I see a guy already!" Caroline unlinked Elena and greeted her boyfriend Tyler Lockwood in the distance.

"That's because you're dating him" Elena's voice trailed off as Caroline left her. Elena cocked her head and smiled at the passionate kiss shared between Caroline and Tyler, they were the perfect couple and Elena really hoped she'd have that one day. Elena realized she was smiling at nothing anymore and still at the entrance, she shook her head and made her way towards the bar where she ordered a diet coke.

"Ahhh, drinking light tonight are we?" Mason Lockwood, Tyler Lockwood's brother asked as he took a seat next to Elena.

"What are you doing here? Don't you have video games at home?" she laughed sarcastically.

"Cheap shot Elena, c'mon let me buy you a drink" Mason insisted, tapping the counter with his hand.

"Is that an invitation to a trip back to your apartment? I hope not Lockwood" Elena smiled sipping her drink through a straw.

"Look, I'm just trying to be nice, not going to come on to you like some dick so just let me buy you a drink, please?" he asked. Elena closed her eyes and inhaled.

"Fine" she slouched in her place giving into his charm.

"Yeah and maybe after this drink we could maybe go have sex in the alley out back" Mason laughed. Elena laughed with him, hitting him with her purse.

"So, how are you?" Elena asked, fixing her dress which was rising up at an inappropriate length.

"I've been good, I've missed you" he said moving closer to her.

"Mason…I've been 7 minuets away from you, you could have just stopped by" she laughed trying to hide her nerves.

"I know but Caroline is always there and if Caroline is there then Tyler is there and I can't catch up with you if my little brother and his girlfriend are making out in the next room" he defended himself poorly, that wasn't always the case, Caroline was never really home, always shopping, going out on dates with Tyler, Elena knew for sure all that being said, Mason was in fact coming on to her.

"Well then talk to me now" she giggled. Ugh, but Elena didn't want to talk, she felt herself suddenly strongly attracted to Mason, just wanted to take him up on his offer for sex in an alleyway. Before Mason could speak, Elena's vodka tonic was set in front of her, she quickly drank, wanting to be drunk enough to maybe even make out with Mason.

"Hey!" Caroline appeared before both Mason and Elena, Tyler's arms wrapped around her waist, he was breathing heavily on her neck making her giggled.

"Hi" Elena said quietly.

"I think it's time for shots" Tyler announced.

"I've been here.." Elena stopped to look at her watch. "10 minuets now and I've got two drinks here" she added folding her arms.

"Ellleeeennnnaaaa" Caroline slurred.

"Fine, okay, whatever" Elena rolled her eyes turning towards the bar, resting her arms on the counter, she could tell Mason's eyes were roaming her body.

"Four tequila shots" Tyler took a seat next to Elena, Caroline on his lap.

They all drank, Elena finishing hers last, they laughed at her.

"Oh shut up!" she buried her face in her hands, pretending to me humiliated.

"Better be prepared Gilbert, we're only getting started" Mason smiled, waving his hand at the bartender for more shots.

2 hours had passed and Elena' neck was wet from spilled tequila which she tried to swallow in recent shot rounds.

"I think that's enough for you" Mason gently held Elena's arm and walked her to the club exited, her purse under his arm he seemed like he was being a gentleman, Elena let him slip his arm around her waist as they strolled out of the club and looked for the nearest taxi rank.

"That was fun" Elena giggled as she stumbled over her own foot.

"Yeah it was but now you have to go home and get some rest" Mason gripped his hands on her tiny waist before she fell to the ground.

"No! I just wan to…" she couldn't finish her sentence.

"What Elena?" Mason asked. Without think, Elena lips were now in contact with Mason's, both of them in shock. She smiled with her eyes still closed before they kissed again, this time she was allowed entry and their tongues massaged each other.

"Come back to my place" she whispered against his ear.

"Well well, the tables have turned" he laughed.

"Just shut up" she threw her arms around his neck. He ran his fingers through her soft brunette locks. They stood in front of a closed clothing store as traffic passed them, as nice as this way Elena couldn't wait anymore, she wanted sex and she wanted it now.

Mason and Elena busted through Elena's apartment door, heading straight to the bedroom, they undressed each other quickly. Elena's dress fell to the floor and now she was standing before Mason in her matching Victoria Secret underwear. She pushed Mason onto the edge of the bed close enough she could still touch him while standing up, she bent down to kiss him again. Mason grabbed Elena's waist and she was now on his lap, her legs wrapped around his waist, her hands touching his bare chest. They kissed again and then Elena was done waiting.

"Fuck me now" she said seductively against his lips. After getting under the covers they both into each other's eyes.

"You're so gorgeous Elena" Mason compliment whilst kissing her neck.

"Okay gotcha" Elena laughed not really caring at any compliment she would receive tonight, she just wanted sex. He was inside of her now. He was bigger then she thought, wait, was she actually having sex with Mason Lockwood? Drunk sex with Mason Lockwood?

"Oh my god" Elena moaned as Mason penetrated deeper into her, she bit her lip to stop from screaming, she wanted this so bad and it was going so much better than she expected. "Harder" she moaned quietly.

"Fuck Elena, you're so wet!" he said, his hands now on her breasts. Wow, thought Elena, this was unlike any sex she had ever had before. There was her first time with high school jock Matt Donovan. Aw, he was sweet, she thought again. High school sweethearts until graduation where he decided to sleep with Dana 'what's her name' at a graduation party. Was she still seriously think about her ex-boyfriend while having sex? She had completely lost it.

_The next morning:_

Elena woke up with a mild hangover. Her arm lay stretched out across the pillow next to her. _Hold on, _she thought. Mason left, how could he just leave like that without even saying goodbye? Elena lifted her head slowly to avoid anymore pain and tied her hair back into a messy, loose ponytail.

"Caroline!", Elena yelled out. No answer. She spent the night at Tyler's again, or else was stranded somewhere in Times Square.

Elena carried her very little strength and got out of bed. She looked down and saw she was only in her underwear. No wonder why she felt so uncomfortable, she never slept in her underwear, but that was the last thing on her mind, she had a one night stand with Mason and then he left. _Work related, _she thought, that had to be it. _Ugh, Elena you're so stupid, he doesn't work on Sundays. _Elena strolled to the kitchen in her bare feet, the cold floor tiles made her shiver. She made herself a cup of coffee to help the few hours of sleep she had gotten last night and sat on her couch with a loud sigh.

Setting her cup on the table before her, Elena then grabbed her latest issue of _Cosmopolitan _and flicked quickly through the pages.

"Find your Prince Charming", Elena quoted the title aloud, rolling her eyes. Stupid magazine, always setting her expectations high, there was no perfect man out there for her and she knew it. Feeling sorry for herself, Elena threw the magazine on the chair across from her and her a key jolt in the door.

"Home!" Caroline squealed, dressed in the same clothes from the night before, her shoes in her hand and her mascara smudged.

"Are you fucking kidding me?" Elena narrowed her eyes at her drunk friend and watched her make her way to her bedroom. Watching drunk Caroline walk was always amusing but Elena didn't laugh this time, she actually felt jealous. Caroline went out on nights and enjoyed herself, she didn't let anything stop her from having a good time, then again she had Tyler.

"I…I have…to go to bed" Caroline struggled to get her words out.

"Understood" Elena nodded in strong agreement.

"Will you help me change?" Caroline asked, puppy eyes displayed. Elena let out yet another sigh and hopped up from the couch, taking Caroline's hand and dragging her to her bedroom.

"No more late nights…or days" Elena shook her head, pulling sweats and a tank top from Caroline's closet. "Here", Elena held out the clothes to Caroline who's head was buried in her folded arms.

"Car…what's wrong?" Elena asked dropping the clothes to the floor and sitting down on the bed pulling the emotional blond into a tight hug.

"It's me and Tyler" she cried. "He was flirting with some…slut last night!" she explained spitting on the word 'slut'. Elena's mouth opened into an 'o' shape as she rocked her roommate back and forth.

"It's gonna be okay, he loves _you _Caroline and only you!" she smiled, trying her best to comfort her. Elena was never good in situations like this, anyone else crying around her just made her feel very uncomfortable.

"You think so?" Caroline lifted her head.

"Of course I do! Remember that time, he brought to Liberty Island and told you he loved you right in front of the Statue of Liberty, your favorite place in the world?", Elena remembered that day perfectly. She had seen her best friend at her happiest that day when she busted their apartment door open and jumped around like a little girl (of course Tyler not there) and ever since then, Elena couldn't wait to plan their wedding.

"He was so sweet then…I just feel like the connection we have is gone, you know?" Caroline exclaimed, wiping her tears.

"I understand", Elena lied, when had she ever had a legitimate relationship, with Matt but that was just like good friends hanging out and the occasional kiss. "C'mon, let's get you in bed" she added, patting Caroline's back. Caroline obeyed and got under her covers, quickly drifting to sleep. Elena pushed back Caroline's straw like hair and left the bedroom. She'd always bee there for her best friend.

A/N: **Oh my god, that last paragraph was hard to write, sorry for the long update wait and here's a long chapter for you guys…yes smut** **between Elena and Mason (don't ship them though) so no it's not 100% delena like I said :/ sorry . Don't worry Damon will be in the next chapter and him and Elena meet - well I won't give anything else away but please review (keeps me motivated)**


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